Acetone → 2,3-Dihydro-1H-indene-1,2-diol

HRID 2394225Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2394225
[CH2:1]1C2[C:4](=[CH:5][CH:6]=CC=2)[CH:3]=[CH:2]1.[CH3:10][C:11]([CH3:13])=[O:12].C[N+]1([O-])CC[O:18]CC1.S(S([O-])=O)([O-])(=O)=O.[Na+].[Na+]>O.C(Cl)(Cl)(Cl)Cl.[Os](=O)(=O)(=O)=O.C(O)(C)(C)C>[OH:12][CH:11]1[C:13]2[C:2](=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:1][CH:10]1[OH:18]

Komponenten

9

Edukt 4

HCID 180AcetoneHCID 7219IndeneHCID 82029Methyl morpholine oxideHCID 656671Sodium Pyrosulfite

Produkt 1

HCID 5211972,3-Dihydro-1H-indene-1,2-diolAusbeute 97 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 30318Osmium TetroxideKatalysatorHCID 962WaterLösungsmittel2×HCID 5943Carbon TetrachlorideLösungsmittelHCID 6386tert-ButanolLösungsmittel

Versuchsvorschrift

To a stirred solution of indene (0.5 g, 4.3 m mol), in a mixture of water (2.5 cm3), acetone (5 cm3) and tert-butanol (1.5 cm3), was added 4-methylmorpholine-N-oxide (0.6 g, 5.9 mmol) and a solution of osmium tetroxide in carbon tetrachloride (0.005 g/0.5 cm3). After stirring the reaction mixture for three days, at ambient temperature, a saturated aqueous solution of sodium metabisulphite (0.5 cm3) was added and the stirring was continued for another hour. The reaction mixture was diluted with water (50 cm3), extracted with ethyl acetate (2×50 cm3) and dried (Na2SO4). Distillation of the solvent, from the organic extract, under reduced pressure, gave crude racemic (1R:2S/1S:2R) 1,2-dihydroxy-1,2-dihydroindene as off-white fluffy crystals (0.63 g, 97%) m.pt. 98°-100° C.

Aufarbeitung

  1. waitthe stirring was continued for another hour
  2. extractionextracted with ethyl acetate (2×50 cm3)
  3. dry with materialdried (Na2SO4)
  4. distillationDistillation of the solvent

Quellen und Nachweise

ORD-Eintrag
ord-bd2dc7f0fdb147f8bccd23a2b5acb765
Quelldatensatz
uspto-grants-1998_09
Patentnummer
US05811294

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